Feedback-driven massive outflows play a crucial role in galaxy evolution by regulating star formation and influencing the dynamics of surrounding media. Extracting outflow properties from spectral lines is a notoriously difficult process for a number of reasons, including the possibility that a substantial fraction of the outflow is carried by dense gas in a very narrow range in velocity. This gas can hide in spectra with insufficient resolution. Empirically motivated analysis based on the apparent optical depth method, commonly used in the literature, neglects the contribution of this gas, and may therefore underestimate the true gas column density. More complex semianalytical line transfer (e.g., SALT) models, on the other hand, allow for the presence of this gas by modeling the radial density and velocity of the outflows as power laws. Here we compare the two approaches to quantify the uncertainties in the inferences of outflow properties based on 1D “down-the-barrel” spectra, using the UV spectra of the CLASSY galaxy sample. We find that empirical modeling may significantly underestimate the column densities relative to SALT analysis, particularly in the optically thick regime. We use simulations to show that the main reason for this discrepancy is the presence of a large amount of dense material at low velocities, which can be hidden by the finite spectral resolution of the data. The SALT models in turn could overestimate the column densities if the assumed power laws of the density profiles are not a property of actual outflows.